J. Environ. Eng. Manage.

, 19(5), 277-282 (2009) 277

ELECTRO-FENTON DEGRADATION OF SYNTHETIC DYE MIXTURE: INFLUENCE
OF INTERMEDIATES
Vahid Vatanpour,
*
Nezamaddin Daneshvar and Mohammad Hossein Rasoulifard
Water and Wastewater Treatment Research Laboratory
Department of Applied Chemistry
University of Tabriz
Tabriz, Iran
Key Words: Electrochemical advanced oxidation processes (EAOPs), malachite green, orange II,
hydroquinone-like intermediates, wastewater treatment
ABSTRACT
Electro-Fenton process is a potentially useful oxidation process for destroying toxic organic
compounds in aqueous medium. In this study, the electro-Fenton degradation of a solution mixture
of Malachite Green (MG) and Orange II catalyzed by ferric ions was examined. Results showed that
this system could degrade and mineralize the dye mixture. It was shown that absorbance decrease in
MG was accelerated in the presence of Orange II, whereas absorbance decrease of Orange II at the
same conditions was depressed. This behavior was attributed to generation of hydroquinone-like
intermediates from degradation of Orange II that can accelerate Fenton reaction by reduction of Fe
3+

to Fe
2+
ions. GC-MS detection of the products formed in the Orange II electro-Fenton degradation
showed the generation of dihydroxynaphthalene compounds that are probably responsible for
acceleration of MG degradation.

*Corresponding author
Email: vahidvatanpoor@yahoo.com
INTRODUCTION

Rapid industrialization and urbanization result in
the discharge of large amount of waste to the envi-
ronment, which in turn creates more pollution. The
majority of colored effluents are caused by the release
of dyes to the environment from textile, dyestuff, and
dyeing industries. Color is usually the first contami-
nant to be recognized in wastewater. A very small
amount of dye in water (10-20 mg L
-1
) is highly visi-
ble and affects water transparency and gas solubility
of waterbodies [1].
Many industrial and agricultural activities use
water in an excessive way. However, it is now well
known that the fresh water resources are limited, so
they must be protected. The availability of clean water
for various human needs in the next decades seems to
become a challenge to take up. There are many classes
of dyes such as acidic, basic, neutral, azo, disperse, di-
rect, reactive, etc. Out of these dyes, azo dyes are
most frequently used. These dyes contain one or more
azo bonds (N=N) in their structure [2]. Triphenyl-
methane dyes are the next in the list. Some of these
dyes are toxic and potentially carcinogenic [3]. About
15% of dyes of the total world production are lost dur-
ing synthesis and processing with wastewater [4].
Thus, there is an urgent need for textile industries to
develop effective methods of water processing.
Many studies have reported decoloration of solu-
tions containing only one dye by different methods.
However, industrial effluents usually contain mixture
of dyes. As a result, investigation of treatment of real
wastewater or mixture of dyes is important.
Development of the appropriate techniques for
treatment of mixture of dyes wastewater is important
for the protection of natural waters. To eliminate dyes
from aqueous colored effluents and reduce their eco-
logical consequences, several biological, chemical and
electrochemical techniques have been proposed: an-
aerobic/aerobic degradation [5,6], Fentons reagent [7],
TiO
2
photocatalyst [8], electro-coagulation/electro-
flocculation [9] and anodic oxidation [10]. Other
physical/chemical techniques including adsorption [11]
and flotation [12] have also been employed. Physi-
cal/chemical methods do not degrade the pollutants
but they only transfer them from the liquid phase to
the solid phase, thus causing secondary pollution.
Conventional wastewater treatment based on biologi-
278 J. Environ. Eng. Manage., 19(5), 277-282 (2009)

cal process is not efficient enough to remove recalci-
trant dyestuffs from effluents, because high molecular
weight compounds are not easily degraded by bacteria
[13]. Despite the high oxidative efficiency of Fentons
reagent, its application is limited by the storage and
shipment of concentrated H
2
O
2
solutions and the gen-
eration of Fe(III) sludge.
Therefore, it is necessary to find an effective
wastewater treatment capable of removing color and
degrading toxic organic compounds from industrial
effluents. As an alternative, an indirect electrochemi-
cal process for decoloration of wastewater containing
dyes is proposed. The electric current induces redox
reactions upon the electrodes surface resulting in the
formation of reactive intermediates that could destruct
the organic compounds. It makes the treatment of liq-
uids, gases and solids possible; it is compatible with
the environment because the main reagent, the elec-
tron, is a clean one [14]. In situ electrochemical pro-
duction of H
2
O
2
in acidic media and regeneration of
Fe(II) by the simultaneous reduction of oxygen and
Fe(III) on a cathode surface can solve the problems of
Fentons reagent. In electro-Fenton process, Fe
2+
or
Fe
3+
ions are added to the solution and hydrogen per-
oxide is electrogenerated from the two-electron reduc-
tion of O
2
on the cathode of an undivided electrolytic
cell [15,16]:
O
2
+ 2H
+
+ 2e

H
2
O
2
(1)

Fenton reaction involves several sequential reaction
steps according to which hydroxyl (

OH) and hydrop-

eroxyl (

2
HO ) free radicals are the key intermediates
in the reaction. The free radical mechanism consists of
the following steps [17]:
Fe
2+
+ H
2
O
2
Fe
3+
+

OH + OH

(2)

OH + H
2
O
2
H
2
O +

2
HO

(3)
Fe
3+
+

2
HO Fe
2+
+ H
+
+ O
2
(4)
Fe
2+
+

2
HO Fe
3+
+ HO
2

(5)
Fe
2+
+

OH Fe
3+
+ OH

(6)
Electro-Fenton process has been used for decoloration
of single-dye solutions such as Acid Red 14 [18], in-
digo carmine [19], direct Orange 61 [20], Malachite
Green [21] and other dyes [22,23]. Note that only two
recent studies reported removal of mixture of dyes by
electro-Fenton [24,25].
The present work studied the decoloration and
mineralization of mixture of two dyes Malachite
Green (MG) and Orange II from two different group
of triphenylmethane and azo, respectively by electro-
Fenton process. Effect of presence of one dye on re-
moval of another dye and influence of initial concen-
tration of counter dye on decoloration of another dye
were examined.

MATERIALS AND METHODS

1. Chemicals

MG and Orange II were purchased from Merck
(Germany) and used without further purification.
HClO
4
(70%), HNO
3
(65%), NaClO
4
H
2
O and
Fe(NO
3
)
3
9H
2
O were obtained from Merck. NaOH
was purchased from Fluka.

2. Instruments

Electrolyses were performed with a DC power
supply. The cell voltage was determined with a UNI-T
(UT2002) digital multimeter. The solution pH was
measured with a Metrohm 654 pH-meter. The dyes
spectra were obtained by using a Lightwave S 2000
UV-Vis spectrophotometer in wavelength of 484 nm
for Orange II and 619 nm for MG. For GC-MS analy-
sis, a GC system (Agilent 6890) with a 30 m 0.25
mm HP-5 capillary column coupled with a HP 5989A
mass spectrometer operating in electron ionization
mode at 70 eV was used. TOC values were deter-
mined by catalytic oxidation with a Skala-Formics
TOC analyzer. All samples were filtered (0.22 m)
and acidified with HNO
3
, (1% HNO
3
, 2 mM).

3. Electrolytic System

The experiments were conducted at room tem-
perature in an open, undivided and cylindrical glass
cell of 400 mL capacity and performed at constant po-
tential. The commercial graphite felt (thickness = 0.4
cm) with 9.5 cm
2
surface area was selected as cathode.
Carbon is widely used as a cathode material for hy-
drogen peroxide generation because it exhibits a range
of electrochemical activities towards oxygen reduction,
high overpotential for hydrogen evolution and low
catalytic activity for hydrogen peroxide decomposi-
tion [26]:
H
2
O
2
+ 2H
+
+ 2e

2H
2
O (7)
The Pt sheet of 1 cm
2
area was used as anode and
the reference electrode was a saturated calomel elec-
trode (SCE). In all experiments, solutions were stirred
magnetically at 600 rpm. Prior to the electrolysis, pure
O
2
was bubbled for 10 min through the solution. Dur-
ing electrolysis, O
2
was sparged at 20 mL min
-1
. Solu-
tions of 200 mL containing one or two dyes (C
0
= 10
-5

M) in 0.05 M NaClO
4
at initial pH 3.0 were per-
fromed by applying a constant potential of -0.5 V. The
conditions for this work were optimized from the pre-
vious work [27]. The value of pH 3.0 was chosen be-
cause several studies [15,16] have shown that the op-
timum pH for Fentons reaction and production of
H
2
O
2
is in the range 2.8-3.0. Before the study of elec-
Vatanpour et al.: MG and Orange II Mixture Treatment by EF 279


0
0.2
0.4
0.6
0.8
1
Time (min)
C
/
C
0
MG
Orange II
0
0.2
0.4
0.6
0.8
1
1.2
0 50 100 150 200
T
O
C
/
T
O
C
0
(a)
(b)


Fig. 1. Removal of an aqueous mixture of dyes MG and
Orange II (C
0
= 10
-5
M of each dye) during electro-
Fenton treatment in the presence of Fe
3+
ions as
catalyst. [Fe
3+
] = 10
-4
M, [NaClO
4
] = 0.05 M, pH =
3 and E = -0.5 V vs. SCE. (a) decoloration; (b)
mineralization.
tro-Fenton process, a catalytic amount of 10
-4
M Fe
3+

was added to the solution.

4. Analysis Procedure

Samples were withdrawn from the reactor at
regular time intervals and the removal of color was
evaluated by simultaneous spectrophotometeric de-
termination using mean centering of ratio spectra [28].
This method has been inspired from successive ratio
derivatives of ratio spectra in two steps. The mean
centering method uses mean centering of ratio spectra
instead of derivatives of them. By eliminating deriva-
tive steps, signal-to-noise ratio is enhanced dramati-
cally.

RESULTS AND DISCUSSION

1. Decoloration and Mineralization of a Mixture
Containing MG and Orange II

A mixture of MG and Orange II at initial con-
centration of 10
-5
M for each one was treated by elec-
tro-Fenton process at -0.5 V. Electrochemically gen-
erated hydroxyl radicals react with dye molecules
leading to their oxidation. Figure 1a shows a rapid de-
cay of each dye present in the synthetic dye mixture as
a function of time during the electro-Fenton process.
Results show that degradation of MG is faster than
Orange II.
The oxidizing power of the electro-Fenton sys-
tem to mineralize dye solutions was evaluated from
their TOC decay. Figure 1b shows selected TOC-time
plot for the degradation of the mixture of MG and Or-
ange II solution using 9.5 cm
2
graphite felt cathode. A
continuous TOC abatement was observed attaining
79% of mineralization after 180 min of electrolysis.
TOC decay shows that this electro-Fenton system can
degrade and mineralize organic pollutants.

2. Electro-Fenton Degradation of MG and Orange
II in Separate and Mixed Solution

Figures 2a and 2b show the absorbance decrease
at 619 nm (MG) and 484 nm (Orange II) alone or in
mixed solution. The removal efficiency of both MG
and Orange II was altered in the mixed solution com-
pared with the separate case. In the presence of Or-
ange II, decoloration of MG was accelerated whereas
decoloration of Orange II was reduced to some extent
when MG was present. The depression of the absorb-
ance decrease at 484 nm can be attributed to competi-
tive trap of hydroxyl radicals by MG [29] and the ef-
fect of high concentration of pollutant. However, the
absorbance decrease at 619 nm was surprisingly ac-
celerated in the presence of Orange II. It was men-
tioned that some degradation intermediates obtained
from degradation of aromatic compounds such as
quinone-like compounds could expedite the reduction
of ferric ions to ferrous ions (Eqs. 10 and 11) [29-32].
As a result, rate of Fenton reaction was accelerated.
k = 110
9
M
-1
s
-1
(8)
k = 110
9
M
-1
s
-1
(9)

k = 4.410
2
M
-1
s
-1
(10)
k = 4.410
4
M
-1
s
-1
(11)

k = 110
9
M
-1
s
-1
(12)

280 J. Environ. Eng. Manage., 19(5), 277-282 (2009)

10
20
30
40
50
60
70
80
90
100
R
e
m
o
v
a
l

E
f
f
i
c
i
e
n
c
y

(
%
)
0
10
20
30
40
50
60
70
80
90
100
0 20 40 60 80 100
Time (min)
only MG
mixed
(a)
(b)
only Orange II
mixed


Fig. 2. Destruction of dyes by electro-Fenton
degradation of: (a) MG, alone or mixed, (b)
Orange II, alone or mixed. [MG] = 10
-5
M,
[Orange II] = 10
-5
M, [NaClO
4
] = 0.05 M, pH =
3.0, [Fe
3+
] = 10
-4
M and E = -0.5 V.

It can be hypothesized, based on what observed
for Fenton systems, that Orange II or some intermedi-
ates generated in the degradation of Orange II could
accelerate the removal of MG by accelerating of hy-
droxyl radical production.
In order to show whether hydroquinone-like in-
termediates generated in degradation of Orange II or
not, electro-Fenton degradation intermediates of Or-
ange II alone was determined after 60 min electrolysis
by GC-MS analysis. Results were reported in previous
work [27]. It is observed that one of the identified in-
termediates is 1,2-dihydroxynaphthalene. It was re-
ported that ortho-dihydroxy aromatic compounds such
as catechol and 2,3-dihydroxybenzoic acid can reduce
ferric ions to ferrous ions [32,33]. Probably generated
1,2-dihydroxynaphthalene from degradation of Or-
ange II can reduce Fe
3+
to Fe
2+
and therefore, lead to
increasing of absorbance decrease rate at 619 nm in
electro-Fenton process.
Generally speaking, in electro-Fenton system
Fe
2+
is regenerated through the reduction of Fe
3+
in
cathode surface (Eq. 13) and then reduced to Fe
2+
by
H
2
O
2
(Eq. 14). However, at the same time in the pres-
ence of hydroquinone-like intermediates, regeneration
of Fe
2+
is prompted and causing a rapid degradation of
contaminant.
Fe
3+
+ e

Fe
2+
(13)
0
10
20
30
40
50
60
70
80
90
100
0
10
20
30
40
50
60
70
80
90
100
0 20 40 60 80 100 120
Time (min)
R
e
m
o
v
a
l

E
f
f
i
c
i
e
n
c
y

(
%
)
(a)
(b)


Fig. 3. Effect of one dye on the other: [NaClO
4
] = 0.05
M, pH = 3.0, [Fe
3+
] = 10
-4
M and E = -0.5 V. (a)
Influence of Orange II concentration on MG (619
nm) at [MG] = 10
-5
M; (b) Influence of MG
concentration on Orange II (484 nm) at [Orange
II] = 2 10
-

5
M.

Fe
3+
+ H
2
O
2
Fe
2+
+

2
HO + H
+
(14)

3. Influence of Initial Orange II Concentration on
MG Degradation

With regard to these findings, that Orange II is
source of hydroquinone-like intermediates, investiga-
tion of the effect of the Orange II initial concentration
on MG degradation is examined. Figure 3a shows that
removal efficiency of MG increased by increasing Or-
ange II concentration up to 2 10
-5
M. This effect can
be attributed to more conversion of Fe
3+
to Fe
2+
by in-
creasing of produced intermediates from degradation
of Orange II. However, at higher Orange II concentra-
tion, scavenging of hydroxyl radicals overcome in ac-
celerating effect and therefore, removal efficiency of
MG is reduced.

4. Influence of MG Concentration on Orange II
Degradation

In previous sections, it was observed that ab-
sorbance decrease at 484 nm (Orange II) in the pres-
ence of MG was depressed. Figure 3b shows that by
increasing MG concentration, removal efficiency of
Orange II is lower. It can be attributed to high scav-
: No Orange II
: 10
-5
M
: 2 10
-5
M
: 3 10
-5
M
: No MG
: 10
-5
M
: 2 10
-5
M
: 3 10
-5
M
Vatanpour et al.: MG and Orange II Mixture Treatment by EF 281

enging of

OH by high concentration of MG, which

reacts quicker with OH, as shown in Fig. 1.

CONCLUSIONS

This paper has considered the electro-Fenton
treatment of mixture of two dyes using in situ hydro-
gen peroxide produced by oxygen reduction on graph-
ite-felt cathode. Experimental results showed that:
Removal efficiency of dyes is attributed to their
structure. At the same conditions, degradation of
MG is faster than Orange II.
Aromatic compounds can catalyze the Fenton reac-
tion when they are transformed into hydroquinone-
like intermediates by hydroxyl radicals. Hydro-
quinone-like compounds promote the Fenton reac-
tion by accelerating the regeneration of ferrous ions,
which is the slow step (Eq. 9) in the mechanism of
the simple Fenton reaction.
GC-MS analysis and degradation rate of MG in the
presence of Orange II show that one of the gener-
ated intermediates of Orange II degradation proba-
bly can accelerate the regeneration of Fe
2+
from re-
duction of Fe
3+
and therefore, lead to acceleration
of MG degradation.

ACKNOWLEDGMENTS

The authors would like to express their gratitude
to the University of Tabriz, Iran for the financial sup-
port and assistance and thank Mr. Mahmoud Zarei for
running the GC-MS experiments and Mr. Jafarizad for
TOC analysis.

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Discussions of this paper may appear in the discus-
sion section of a future issue. All discussions should
be submitted to the Editor-in-Chief within six months
of publication.
Manuscript Received: March 28, 2008
Revision Received: June 18, 2008
and Accepted: June 18, 2008